Pyridine → HCID 178483592, compound

HRID 557628Notes

Reaction equation

HRID 557628 reaction equation
[CH:1]([O:4][C:5]([C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].ClC(Cl)C.S(Cl)(Cl)=O.[CH2:33](N)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([NH-])C1C=CC=CC=1.C[O:50][C:51](=[O:57])[CH:52]=[C:53]([NH:55][CH3:56])[CH3:54].N1C=CC=CC=1>C(#N)C.C1COCC1.CN(C=O)C>[CH2:33]([O:57][C:51]([C:52](=[C:53]([NH:55][CH3:56])[CH3:54])[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:7]3([C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:6])[CH2:8][CH2:9]3)=[CH:11][CH:12]=2)=[CH:21][CH:20]=1)=[O:23])=[O:50])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

11

Reactant 7

HCID 1049PyridineHCID 63651,1-DichloroethaneHCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 2734182Methyl 3-(methylamino)but-2-enoateHCID 22619318Benzyl amideHCID 666604224'-(1-(Isopropoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid

Product 1

HCID 178483592HCID 178483592, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4′-(1-(Isopropoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid (9.2 g, 28 mmol), dichloroethane (50 mL), DMF (0.1 mL), thionyl chloride (5.5 mL, 62 mmol) were heated to 75° C. for 1.5 hours. (acid chloride formation was monitored by adding small aliquot (100 μL) to a solution of benzyl amine in acetonitrile and analyzing for the benzyl amide by LCMS; no starting material was observed by LCMS). The solution was evaporated on a rotavap and THF (10 mL) was added. The solution of the acid chloride in THF was added via syringe to a solution of 3-methylamino-but-2-enoic acid methyl ester (4.0 g, 31.2 mmol) and pyridine (5.5 mL, 70 mmol) in THF (50 mL). The solution was stirred at room temperature overnight. The volatiles were evaporated on a rotavap to yield the crude product.

Workup

  1. customThe solution was evaporated on a rotavap
  2. additionTHF (10 mL) was added
  3. customThe volatiles were evaporated on a rotavap

Sources & evidence

ORD record
ord-b75e58b0bded49de989d259c014b88cf
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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